Patent GB-814511-A (GB)
Title: Process for the manufacture of polyglycidyl ethers of polyhydroxy-1:3:5-triazines
IPC: C08G59/04
Filed: 1957-06-25
Abstract: Polyglycidyl ethers of polyhydroxy-1 : 3 : 5-triazines are obtained by reacting epichlorhydrin with the polyhydroxy triazine in the presence of a solid dry compound binding HCl, e.g. sodium or potassium hydroxide or carbonate, or alkali metal aluminates, zincates or silicates.  The process is effected by heating the reactants in the presence of the dry compound under reflux and removing the water as it is formed.  The products are admixed with triazines containing chlorhydrin groups which may be reduced by a mild treatment with alkali, e.g. with a solution of KOH in methanol. Triazines specified are 2-chlor-4,6-dioxy-triazine, 2-phenyl-4,6-dioxy-triazine (benzoguanamide), 2 - amino - 4,6 - dioxytriazine (ammelide) and cyanuric acid.  The polyglycidyl ethers may be hardened by heating alone or with known hardening agents, e.g. amines, carboxylic acids and their anhydrides.  The products can be used with hardeners in solution as impregnating agents for cellulosic polyamide, polyacrylonitrile, or polyester fabrics or as coating compositions for glass metals and wood; as thickeners for printing pastes or inks; as adhesives and as stabilizers for polyvinyl halides and as modifiers for acrylic, vinyl, polyesters, aminoplasts and epoxide resins.  In examples, 1 mol. cyanuric acid is heated with 9 mols. epichlorhydrin in presence of 1.5 mol. dry powdered Na2CO3. The water of reaction and excess epichlorhydrin is distilled off azeotropically and the epichlorhydrin recycled.  A product containing 2.7 chlorine equivalents per kg. was obtained which after treatment with KOH in methanol was reduced to 0.60 equivalents; (4) 0.1 mol. benzoguanamide is treated with 0.8 mol. epichlorhydrin under similar conditions.ALSO:Polyglycidyl ethers of polyhydroxy-1 : 3 : 5-triazines admixed with 1 : 3 : 5-triazines containing chlorhydrin groups are obtained by reacting epichlorhydrin with a polyhydroxy-1 : 3 : 5-triazine in the presence of a solid dry compound capable of binding HCl., e.g. sodium carbonate, sodium hydroxide, potassium carbonate or an alkali metal aluminate, silicate or zincate.  The process is effected by heating the reactants in presence of the dry compound under reflux and removing the water as it is formed. Polyhydroxy 1 : 3 : 5-triazines specified are 2-chloro-4 : 6-dioxy-triazine, 2-phenyl-4 : 6-dioxy-triazine (benzoguanamide), 2-amino-4 : 6-dioxy-triazine, ammelide and cyanuric acid.  The chlorine content of the products may be reduced by mild treatment with an alkali, e.g. by using methanolic potassium hydroxide, which presumably converts chlorhydrin groups to epoxide groups. In examples: (1) 1 mol. of cyanuric acid is heated with 9 mols. of epichlorhydrin in presence of 1.5 mols. of dry powdered sodium carbonate and the product is partly dechlorinated by treatment with potassium hydroxide in methanol; (2) 1 mol. of cyanuric acid is heated with 12 mols. of epichlorhydrin in presence of 1.5 mols. of dry powdered sodium carbonate; (3) a product is obtained as in (2) and is esterified with linoleic acid; and (4) two 0.1 mol. portions of benzoguanide are reacted with 0.8 mol. and 1.0 mol. of epichlorhydrin respectively in presence of 0.1 mol. of dry powdered sodium carbonate.